Dicyclohexylcarbodiimide → N,N'-Dicyclohexylurea

HRID 1954652Notes

Reaction equation

HRID 1954652 reaction equation
CCCCCCCCCCCCCCCC(OC[C@@H](OC(CCCCCCCCCCCCCCC)=O)COC(CCC(O)=O)=O)=[O:17].ON1C(=O)CCC1=O.CN(C1C=CC=CN=1)C.[CH:65]1([N:71]=[C:72]=[N:73][CH:74]2[CH2:79][CH2:78][CH2:77][CH2:76][CH2:75]2)[CH2:70][CH2:69][CH2:68][CH2:67][CH2:66]1>C(#N)C>[C:72]([NH:71][CH:65]1[CH2:66][CH2:67][CH2:68][CH2:69][CH2:70]1)([NH:73][CH:74]1[CH2:79][CH2:78][CH2:77][CH2:76][CH2:75]1)=[O:17]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 80170N-HydroxysuccinimideHCID 1300201,2-Dipalmitoyl-3-succinylglycerol

Product 1

HCID 4277N,N'-Dicyclohexylurea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

The targeted formulation disclosed in Example 11 of commonly owned U.S. application Ser. No. 08/851,780, filed May 6, 1997 (the disclosure of which is incorporated herein by reference), was prepared in the following manner: to a cooled (0 to 5° C.) solution of 1,2-dipalmitoyl-sn-glycero-3-succinate 66.8 mg, N-hydroxy-succinimide 11.5 mg, dimethylaminopyridine (DMAP) 2 mg and acetonitrile 40 mL in a 100 mL round bottom flask was added dropwise to a solution of dicyclohexyl carbodiimide (DCC) 20.6 mg in acetonitrile 10 mL. The resulting mixture was stirred for 5 hours. The solid material which formed during the reaction (dicyclohexylurea) was removed by filtration, and the filtrate was concentrated in vacuo to yield 78 mg of a white product of N-DPGS-succinimide.

Workup

  1. customwas prepared in the following manner

Sources & evidence

ORD record
ord-138b1092a39d4c05943a22d2ad3327b3
Source dataset
uspto-grants-2000_09
Patent number
US06123923

Reaction notes

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